Azo dye.



iii

iJ-ldlillldllil lii ftlllilhltll FICE,

I-QUIS BLANQEY, O1 IMAIil'N'HlilItM, AND CARL IYIIMERHEISER. OF LUDWIGSHAFEN-ON- Tl-IE-RHINE, GERMANY} iitS'iSIGlfllOl't" 550 BADISC'E IE ANILIN J SODA FABRIK, OF

7 reciowlssusrnu-cit-rungs:

Also '1) YR No Drawing.

lit

and lmdwigshutcn-on-thoithinc, illcrmuuy, have invented new and useful in:pr:Wriucuts in Azo Dyes, of which the following is a specification.

"We have discovered that uric colorii'ug unit-- tcrs which are specially suitoblc in thcform of lakes can ho cbtuinci billing a disco compound i'rcc fro; acid, curbcnylic acid and hydro'ryl groups with a chlorinated bcnzoyl-Ld-li-imino-snu ihthol i fi-disulgtonic acid which ci'intuius lit lc'ast onc chloriu atom in tlic bcnzcnc nucleus. In tho form their lid-(cg, cspcci ully tho barium lELllCEBS, thcy arc gcncrully ycl lower and more brillicnt than those oi the non-chlorinated bcnzoyl compounds. he now coloring matters urc charucturizzcd by the fact that on gentle rcduction with stonnous chlorid and hydrochloric cc giro rise to an amino compound fret M0111 sul: ionic acid, carboxylic acid and liydroxy'l groups, and also to an amino dcrivutivc oft u chlormsted bcnzoyl-l.8-ummo-nuphthol-d.6- disulfonic acid containing at least ons chlorin atom in the benzene nucleus. The now yellow-red to violet powders which yield ycllow-rcd tl') VlOl6t solutions in water and,

in the :torn: off their itlkdlinc curth lakes, possess yellow-red to violet shades.

The following cxamplc will sor vc to illustruto further the nature of our invcntiou, which, however, is not confined to this cxample. The parts are by weight.

Diazotizc 127 .5 ports of mctu'cl'ilor-unilin (which may be done in tho usuul. miuuicr) and run the solution, whilc stirring, into it solution of parts of the disodium sult of ortho-para.dichlor-bcmoyl-LS amino-naphtho-4l-.6-disul:tonic acid, to which an crrccss of sodium carbonate has been added, 'Vil1cn the combination isicomplotc, hcut-tlusiinuss to about 80C. and after adding common salt, if necessary, filter oft and press undulry the coloring matter. When dry, it u let powder which yields u brilliiint ycllowred solution in Water and in tho form of its alkaline earth lakes possesses brilliant bluc red shades" Ongentlc reduction with stuu-- Specification of Lcttcrs l sutcut.

Pjtllll vcly, u ll the Swiss Republicand cat the tlcirmuu i lmpire, residing, respectively, t hlunulicuul Paton tcd Sept. 23,1913.

Application lilcd Nov as. 1913. Scrial No. 770 332.

l nous chlorid :md hydrochloric acid, it gives risc to EllQtlll-( ll l()l"lllllllll' undun amino dcrii uti V0 0 '1' mi lio-pu ru-dichlor-bcnzoyl-Li'li muiuo-nuphthol--Htdisultonic acid.

In :1 similarmunncr, coloring matters may be obtained from compounds other than incl:ochlor-unilin; for iustmtccjffom 'aliilin, tho toluidins, xylidins, pseudo-cumidin, 1mcmochlorunilin (oi-tho or para), dichlor- :milins, (l-chlor-2-umino-toluene, unisidins, plici'ictidins, paru-chlor-ortho-anisidin, 01- th o-chlor-pum-uuisidiu, and olphzvnaphthylluniul 'Ilhc ortho para dichlo'r -bcnzoyll.8-mnino-nuphthol- LG-disulfonic acid can ho replaced by -cithcr the ortho-, or the mot-2c, or the para, monochIor-benzoyl-1.8- i'till'ilILO-Il:tphtl1()l-d.tidlSl1lfOI1lC acid.

*lhc conversion of the coloring matters into lakes can be effected in any convenient manner.

Now what we claim is 1. Tho new uzo coloring matters which can bc obtained by combining a dinzo compound which is free from sulfonic acichcarboKylic acid cndshydroxyl groups with a chlorinated bcnz0yl.-1.8-omino-nuphthol-t.6- disulfonic acid containing at least one chlorin atom in the benzene nucleus, which coloring matters consist when dry of yellowrc'd to violet powders which yield yellowrod to violct solutions in water and in the form of their alkaline" earth lakes possess yellow-red to violet shades and which upon gentle reduction with stannous chlorid and hydrochloric acid give rise to an amino compound free from sulfonic acid, carboxylic acid and hydroxyl groups and also to an inf-lino dcrivativc of a chlorinntcd benz'oyl '1.8-mnino-naphtho1-4.6-disulfonic acid containing at least one chlorin atom in the benzcnc nucleus.

2, The new azo coloringrmattcrs which can be obtainlid by combining a diazo compound which is free from sulfonic acid, carboxylic acid and hydroxyl groups with ortho-para-dichloghcnzoyl-lfi amino-naphthol--t6-clisulfonic acid, which coloring inattcrs consist when dry of yellow-red to violet powders. which yield yellow-red to violet solutions in wotcr and in the form of their tion with stmmous chlorid' and ydrochloric ucidgivo rise to an ammo compound frec z llniline carth lakes possess yellow-red to violct shades and which upon entle reduc- Q wzw from sulfonic acicl carboxylic acim and l1y' droxyl gl nups and also to an. amino. derivatfie 5' Of orfi li para-dichlof benzoy1-1 8 amin o-n aphthol-LG-disnlfonic acibl,

3. The new zzz ocol ating nifa tfer obtain able from diazotizecl metzych-l o-l anilin g ngl, ino-nuph hQH- v l tr c0nsisfs hen dry, of a scarlet pbwder which yieldsgbrilliant yellow-red Solution in Water and in the form of its alkaline earth lakes possssesfbrill-iant blue-recl Shades and whibh npqn gentle reduction with stammg (5.111 hands in the presence of two subscribmg WltDGSSGS;

LUUIS BLANGQEYg CARL B iMERHEISER.

lVil nesses J. ALE LLOYD, JOSEPH PFEEFFER. 

